Historically, the Major League Baseball trade deadline has been a 50/50 proposition.
Contenders raid pretenders rosters for top shelf talent, while pretenders mine contenders minor league systems for future help.
Sometimes, the deadline deals work out well. Others, well, let’s just say someone got fleeced.
This year’s deadline is just four days away and there has already been a little bit of movement. With so many teams still realistically in the hunt for at least a wild card spot, expect more.
The Arizona Diamondbacks made the first big move, acquiring J.D. Martinez from the Detroit Tigers for a trio of minor league infielders. The New York Yankees followed suit, picking up 3B Todd Frazier and relievers David Robertson and Tommy Kahnle from the Chicago White Sox for reliever Tyler Clippard and three minor leaguers.
Whether those deals, and the ones to follow, work out remains to be seen.
Here are 15 trade deadline moves over the years that backfired badly, in chronological order.
15. Yankees Trade Jay Buhner To Mariners – 1988
This deal was so infamous, it even got play on the hit comedy “Seinfeld”, where Frank Costanza gives George Steinbrenner the gears for pulling the trigger on it. That trade was the one that sent promising young outfielder Jay Buhner to Seattle for 33-year-old journeyman 1B/DH Ken Phelps. The Yanks were in the hunt for an AL East title that year and needed a veteran bat for the middle of the order. Phelps did punch out 10 homers (22 RBI) in 45 games down the stretch, but New York missed the playoffs anyway and Phelps was out of baseball by 1990. Buhner had 32 games and three homers in the bigs with the Yanks before the deal. He swatted 10 homers in 60 games with the M’s over the remainder of the ’88 season. He would go on to hit 297 more jacks in the next 13 campaigns in Seattle, including three straight seasons (1995-97) of 40 or more homers and 100+ RBI.
14. Boston Sends Curt Schilling And Brady Anderson to Baltimore – 1988
Not long after the Buhner trade in New York, division rival Boston pulled a swap with Baltimore that lives in infamy. First, the biggest rule of thumb isn’t to make big trades in your own division, so the Red Sox broke that one, big time. Boston was in the thick of the race in 1988 and needed a veteran starter to get them over the hump. Baltimore made former 20-game winner and All-Star Mike Boddicker available and Boston was only to happy to include minor leaguer Schilling and then light-hitting rookie outfielder Brady Anderson in the deal. Well, the Bosox did make the playoffs that year and Boddicker pitched well down the stretch, only to get shelled in his lone start in the ALCS (Boston lost the series 4-0 to Oakland). He spent two more years in Beantown and was gone by 1991. While Schilling wasn’t quite an all-star in Baltimore he became huge and later (ironically) win a world championship in Boston. Anderson spent 14 seasons in Baltimore, was an all-star three times and hit 50 homers in 1996. Ouch.
13. Red Sox Deal Jeff Bagwell To Houston – 1990
At least they didn’t trade within the AL East this time. But, had this swap not been pulled off, Jeff Bagwell’s bust in the Hall of Fame would be sporting a Red Sox cap, and not that of the Houston Astros. Now, this trade wasn’t technically a deadline deal (it happened Aug. 30, 1990) but we’ll call it close. At the time, the Red Sox were again in the hunt for a playoff spot and needed relief help, so they contacted the Astros about veteran set-up man Larry Andersen. With Wade Boggs still ensconced at third, minor league 3B Bagwell, then at AA New Britain, was deemed expendable. Andersen was good down the stretch in 15 games but mediocre in the playoffs as Boston again lost to Oakland in the ALCS. He was gone after that half season, too. Bagwell, meanwhile, didn’t take long to blossom in Houston, spending his entire Hall-of-Fame worthy career there. He won Rookie of the Year in 1991 and was MVP in 1994.
12. Toronto Trades David Cone To The Yankees – 1995
File this one under “you don’t know what you got, ’til it’s gone — again.” The Toronto Blue Jays, just two years removed from a World Series title, reacquired 1994 Cy Young winner David Cone from the Kansas City before the start of the ’95 season. Cone had helped the Jays to their first title in 1992 and was dealt back to Toronto for a few minor leaguers. He pitched well in 17 starts that year, going 9-6 with a 3.38 ERA, but the Blue Jays were floundering and looking to unload high-priced help. Enter the Yankees, who had rebuilt themselves after 13 seasons without playoff ball. They would send promising young righthander Marty Janzen and two other minor league arms to Toronto for Cone. He went 9-2 the rest of the way for the Yanks, who finally made the playoffs and would be a key member of the rotation for four championships in the late 1990s. Janzen, the “biggest” return in the deal, spent two years with Toronto and won six games before being out of the big leagues in 1997.
11. Mariners Package Up Derek Lowe And Jason Varitek To Boston – 1997
This time, it was Boston finally getting the upper hand in a deadline trade. Seattle was in the midst of a playoff drive in ’97 and severely needed bullpen help. The Red Sox, who were scuffling, had All-Star reliever Heathcliff Slocumb on the roster and made him available. Only thing was, while he did have 17 saves that season, his ERA was an abysmal 5.79 in 49 appearances. Undaunted, the M’s surrendered minor league catcher Jason Varitek (their first round pick in 1994), as well as young starter/long reliever Derek Lowe to get Slocumb. He was marginally better in a Mariners’ uniform, getting his ERA down to 4.13 and saving 10 more games, but was largely a non-factor in Seattle’s NLDS loss to Baltimore. Varitek was Boston’s full-time catcher by 1999 and would be team captain on two World Series winning Red Sox teams. Lowe was great in the bullpen and as a starter for eight seasons. He saved an AL high 42 games in 2000 and was 3-0 as Boston ended the Curse of the Bambino in the 2004 playoffs.
10. Montreal Trades Away Cliff Lee, Brandon Phillips, Lee Stevens And Grady Sizemore – 2002
Little wonder the Expos faded from relevancy and moved to Washington in time for the 2005 season. In 2002, the Expos were actually fighting for a post-season spot they hadn’t had in 21 years. A proven starter was required, though and the Cleveland Indians were looking to unload Bartolo Colon. So, figuring they had a legitimate shot at a playoff berth, the Expos packaged up minor league prospects Cliff Lee, Brandon Phillips and Grady Sizemore along with slugging 1B Lee Stevens to Cleveland for Colon, who was 10-4 at the time and part-time starter Tim Drew. Colon did win another 10 with Montreal, but they missed the playoffs anyway and then he was dealt again for peanuts in the off-season. Cleveland reaped the rewards, for sure. Lee would win a Cy Young with the Indians in 2008, while Brandon Phillips would mature into an all-star second baseman, albeit in Cincinnati. Sizemore would play eight seasons in Cleveland and slug 139 homers, along with being an all-star in three of them.
9. Pirates Send Aramis Ramirez And Kenny Lofton To The Cubs – 2003
There weren’t many bright shining moments in this century’s first decade for the Chicago Cubs, but the heist they pulled off at the expense of the Pittsburgh Pirates was one of them. For the first time in five seasons, the Cubs were angling for a playoff run in 2003. The Bucs, on the other hand, were in the throes of mediocrity and were looking to unload slugging 3B Aramis Ramirez and veteran outfielder Kenny Lofton. But, they made the faux pas of dealing within their division, sending the two to Chicago for infielder Bobby Hill, utility man Jose Hernandez and minor league pitcher Matt Bruback. Ramirez would become the Cubs powerful third sacker for nine seasons, swatting 239 homers and making the All-Star team twice. He also banged out four homers during the 2003 playoffs, as the Cubs narrowly missed winning the pennant. Speedster Lofton was great down the stretch in his only stint with the Cubs, and hit .307 in the post-season with four stolen bases.
8. Yankees Deal Jose Contreras To White Sox For Esteban Loaiza – 2004
Pitcher for pitcher, this may the worst of this kind of deadline day deal ever. On July 31, 2004, the New York Yankees traded big Cuban righthanded starter Jose Contreras to the White Sox for middling veteran Esteban Loaiza. At the time, however, Contreras was struggling, going 8-5 with a 5.64 ERA in 18 starts. Loaiza, on his fourth team in 10 seasons, was marginally better, sporting a 9-5 record and 4.86 ERA. So, on paper, it looked like a wash. But, after another so-so half season, Contreras went 15-7 in 2005 and shaved his ERA down two full points to 3.61. In the ’05 post-season, Contreras was 3-1 in five starts, recording a 2.53 ERA to help the White Sox win a World Series title. Loaiza, for his part, was 1-2 in 10 games (six starts) and had a dismal 2.055 WHIP for the Yanks. He was gone after that season.
7. Milwaukee Swaps Nelson Cruz And Carlos Lee To Texas – 2006
It seems like the Milwaukee Brewers are forever in sell mode. They have made the playoffs exactly twice since 2003 and usually find themselves at a position of vulnerability at the trade deadline. It was no different in 2006, as they scuffled through yet another sub .500 campaign. Having offered a rich extension to slugger Carlos Lee that year, the Brewers decided to cut bait rather than lose him in free agency, sending him and minor league outfielder Nelson Cruz to the Texas Rangers for outfielders Kevin Mench and Laynce Nix, reliever Francisco Cordero and a minor league hurler. Lee hit well down the stretch for Texas in a non-playoff year (.322, 9 HR, 35 RBI) but would sign with Houston in 2007. Cruz took a little time to percolate in the Rangers organization, but by 2009 he was an All-Star and over the course of eight seasons in Texas he would hit 157 home runs. Mench and Nix never did much for the Brew Crew and after one good season closing for Milwaukee (44 saves in 2007), Cordero was gone.
6. Pittsburgh Tanks In Three-Way Deal With Dodgers And Red Sox – 2008
In this infamous deadline trade in 2008 the Boston Red Sox got all-star outfielder Jason Bay and the Los Angeles Dodgers received enigmatic Manny Ramirez. Pittsburgh, well, they got OF Brandon Moss and P Craig Hansen from the Bosox and 3B Andy LaRoche and P Bryan Morris from L.A. Bay fit in well in Beantown for a season and a half, having his best career season in 2009 when he hit 36 homers and drove in 119 runs. Man Ram hit a lofty .396 in the latter part of 2008 with the Dodgers, along with 17 homers and 53 RBI. He also went a ridiculous 13-for-25 in two post-season series for L.A., with four dingers and 10 RBI. Brandon Moss did nothing for the Pirates and broke through later for Oakland, while Andy LaRoche never quite lived up to his famous brother’s lofty totals, either. Hansen lasted just 21 games in Pittsburgh and was out of the big leagues in 2009 and Bryan Morris was actually the best of the bunch, appearing in 81 games over three seasons and registering a 3.46 ERA.
5. Padres Give Away Cory Kluber In Three-Team Swap – 2010
Imagine being Padres management in 2014 and your team is in the midst of yet another sub-par year, while having to watch former farmhand Cory Kluber cop Cy Young honors in the American League with the Cleveland Indians. Four years earlier, that very same management agreed that Kluber, a minor league prospect, was expendable and engineered a three-team swap that saw St. Louis get Cleveland starter Jake Westbrook and Padres pitching prospect Nick Greenwood. The return for San Diego? Former all-star outfielder Ryan Ludwick from the Cards. He was only a shadow of his All-Star self in 160 games with the Pads, hitting a dismal .228 with 17 homers. Westbrook helped St. Louis win a championship in 2011, while Greenwood had a cup of coffee with the team over two seasons.
4. Rangers Trade Chris Davis And Tommy Hunter To Baltimore For Koji Uehara – 2011
On paper at least, this trade didn’t look all that bad when the Texas Rangers and Baltimore Orioles completed it at the deadline in 2011. The Rangers, coming off a World Series loss to San Francisco, were loading up for another run and needed a middle reliever/closer of Uehara’s pedigree in their bullpen. At that time, Davis was a good defensive first baseman and Tommy Hunter showed promise as a reliable, un-flashy starter. Uehara was decent in just 59 total games with the Rangers, but was roughed up considerably in the playoffs, giving up five earned runs in just 1.1 innings pitched. Davis went to a struggling Baltimore franchise and began mashing the ball like a champ in 2012, hitting 33 homers. In 2013, he led the AL in homers (53) and RBI (138) and has ripped 216 big flies and counting. Hunter made a good transition from starter to middle reliever with the O’s and pitched in 224 games, logging a 4.16 ERA and saving 15. A win-win for Baltimore.
3. Boston Deals John Lackey To St. Louis For Allen Craig and Joe Kelly – 2014
The Red Sox won their third championship in nine years in 2013, largely due to contributions from veterans like pitchers John Lackey and Jon Lester. But, like a lot of champions, they swooned the next season and at the deadline the fire sale was on. First they sent Lester (2-0 in ’13 world series) to Oakland and hours later shipped Lackey (1-1, 2.57 ERA in ’13 world series) to St. Louis for All-Star outfielder Allen Craig and pitcher Joe Kelly. Lackey ended up being very good in St. Louis, going 16-13 in 43 starts over a season and a half with a 3.10 ERA. He also helped the Cardinals make it to the playoffs in 2014 and again in 2015, starting four more games and going 2-0. Craig, a great hitter in St. Louis for five seasons (.291 BA, 57 HR, 291 RBI) tanked spectacularly in Boston, hitting just .139 in 65 total games. The saving grace for Boston is the fact Kelly is still with the team, but only in a middle relief role.
2. Oakland Trades Away Addison Russell Ahead Of Deadline – 2014
When the A’s aren’t in the running for the playoffs, it’s a fire sale in the Bay Area at deadline time. However, when they are in the mix, they have made some dubious deals. In 2014, they needed starting pitching to propel them into the Big Dance and pulled the trigger on a big trade with the Chicago Cubs that netted them Jeff Samardzija and Jason Hammel. The Cubs stocked the shelves by getting top prospect shortstop Addison Russell, righthanded pitcher Dan Straily and young outfielder Billy McKinney. Oakland did make the playoffs in ’14, but neither Samardzija or Hammel were a factor, as they lost the wild card game to Kansas City. They both turned out to be rentals, as Hammel went back to the Cubs in free agency after the 2014 season and Samardzija joined crosstown rival White Sox in a off-season trade. That rental had a steep price, as Russell has become an All-Star, world champion and the everyday shortstop people expected him to be. McKinney is now in the New York Yankees farm system and Straily is still in the bigs with Miami.
1. San Francisco Pays A High Price For Rental Mike Leake – 2015
The Gigantes have been uber-successful this decade, winning three championships between 2010 and 2014, so they can be forgiven for making deals to go for it — even if things don’t pan out. Yet, in 2015, they paid a hefty price to obtain starter Mike Leake from Cincinnati at the deadline. Leake was 9-5 with a 3.56 ERA in 21 starts for the Reds in 2015 when he was dealt to the Giants help them push for another playoff appearance and defend their 2014 title. It didn’t work out, as Leake went 2-5 the rest of the way and was gone to St. Louis in free agency at the conclusion of the season. And the players the Reds got? None other than Adam Duvall was one of them. After a brief debut in 2015, he exploded last year, clubbing 33 homers and driving in 103 runs. Currently, the All-Star outfielder/first baseman has 28 doubles, two triples and 21 homers, along with 68 RBI.